Payroll and Benefits Specialist

Two Chairs is building a new kind of mental health system based on the idea that the status quo isn’t good enough. Industry-best clinician experiences, better client outcomes, groundbreaking innovation, and access to the highest quality care are how we’ll raise the bar for the entire industry. With that, we're excited and honored to have been recognized as a 2025 Great Place to Work and 2025 Fortune’s Best Workplaces in Healthcare.

One of our company values is "Embrace Differences" and diversity, equity, inclusion, and belonging are the principles guiding how we build our business and teams. We encourage interested candidates from all backgrounds to apply even if they don't think they meet some expectations of the role.

About the role

We’re looking for a detail-oriented Payroll & Benefits Specialist to join our People Operations team. In this role, you’ll help keep our payroll and benefits operations running smoothly while supporting employees across a growing number of states. You’ll own day-to-day payroll execution, assist with benefits administration and compliance processes, and serve as a go-to resource for employee questions, helping create a seamless employee experience.

You’ll gain hands-on experience across payroll preparation, benefits administration, compliance audits, and core HR operations while also contributing to People Operations projects that improve and scale our processes. This is an exciting opportunity for someone who cares about accuracy, enjoys building efficient systems, and is eager to grow a long-term career in People Operations.

Core Areas of Responsibility 

• Payroll Execution
• Process bi-monthly company-wide payroll, ensuring accuracy, timeliness, and compliance 
• Review, verify, and reconcile timecard data (hours, OT, paid time off, and leave of absence balances)
• Serve as the primary point of contact for employee questions regarding paychecks, deductions, and tax withholdings
• Calculate and process bonuses, retroactive pay, and final paychecks for terminating employees
• Compliance and Operations 
• Manage state registration and employment taxes through our HRIS and in partnership with local municipalities
• Recommend improvements to Two Chairs’ current payroll procedures for increased scalability and accuracy as we expand into new, more complex markets
• Ensure all payroll processes align with federal, state, and local labor laws and tax regulations
• Support internal and external payroll audits (e.g 401k 5500)
• Partner closely with Finance and People Business Partners on payroll-adjacent workflows including leaves, terminations, and some benefit-related needs
• Benefits & Compliance Support
• Provide first-line support for employee questions regarding health, dental, vision, FSA/HSA, 401(k).
• Assist with benefits enrollments, life event updates, and employer offerings by coordinating with external vendors.
• Conduct audits of benefits data to ensure accuracy in billing, eligibility, and payroll deductions.
• Support compliance activities, including ACA reporting, 401(k) audits, and state/federal requirements.
• Partner with brokers, vendors, and internal stakeholders to research and resolve benefits discrepancies.
• People Operations & Employee Support
• Respond to employee inquiries through the People Team ticketing system, ensuring accurate and timely resolution.
• Provide support across a wide range of People Operations workflows—including onboarding, offboarding, and transfers—by ensuring payroll, benefits, and employee data are accurate and up to date. This role also offers opportunities to contribute to process improvements and cross-functional projects.
• Maintain accurate employee records and documentation across HRIS, payroll, and benefits platforms.
• Support reporting and data needs by building and maintaining standard People Operations reports, assisting with audits, and ensuring leadership has accurate, timely insights into payroll, benefits, and employee data.

Impact and Success Indicators 

Where you’ll make an impact in the first 90 days:

• Learn the business — understand the employee population (exempt, non-exempt, full/part-time clinicians, variable pay, etc.) well enough to anticipate issues before they surface
• Process each payroll cycle on time and accurately from day one to establish critical and foundational trust
• Review and build on the source of truth documentation following a complete benefits and payroll data audit
• Begin centralizing payroll and benefits operations within the function

 Where you’ll make an impact in the first year:

• Reduce paycheck-related inquiries and escalations, not just errors
• Ensure multi-state compliance is proactive, not reactive, by tracking and handling new state registrations, tax changes, and mandated updates before they become problems
• Move the department toward meaningful scalability improvements related to payroll and benefit workflows and documentation
• Ensure benefits open enrollment runs smoothly end-to-end

We’re looking for someone with:

• At least 2 years of experience in an HR role at a startup or fast-paced company environment
• Experience supporting payroll and affiliated state taxes - Rippling experience strongly preferred
• Strong attention to detail with a desire to enhance processes for scalability
• Ability to work independently and multitask
• Thrive and live by operational excellence - you’re able to prioritize across many stakeholders without dropping the ball
• Great team player with a collaborative approach
• Strong technical, analytical, written, and verbal communication skills
• Highly organized and able to stay on top of tasks in a complex environment
• Comfortable operating with ambiguity in a complex environment, and escalating appropriately when needed
• Working knowledge of federal and state wage and hour laws, with experience navigating multi-state compliance

Compensation & Benefits

The offer range is dependent on qualifications and experience. New hires can reasonably expect an offer between $70,000-$85,000. 

Additional perks and benefits:

• Equity in a high-growth start-up
• Paid time off, including nine paid holidays and an additional Winter Office Closure from Christmas Day (Observed) through New Year's Day
• Comprehensive medical, dental, and vision coverage
• 401(k) Retirement savings options
• One-time $200 Work from Home reimbursement
• Annual $1,000 Productivity & Wellness Stipend to support your personal and professional goals
• Annual $500 subsidized company contribution to your healthcare FSA or HSA
• Paid parental leave

Outreach Notice to Applicants

We are thrilled that you’re interested in joining our team! To ensure a consistent and equitable hiring process for all candidates, we kindly ask that you refrain from reaching out to current employees regarding the role, your application, or the interview process. Our talent acquisition team is committed to carefully reviewing all applications and will reach out directly if they decide to move forward.

If you need a reasonable accommodation, please let your recruiter know so our People Team can assist you.

All applicants must be authorized to work for ANY employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.